Helping him make his "First Move" with me...

Ask him if he would like to do an event or class together with you. Dancing classes would be best. Maybe some ballroom dancing? Anything with casual, friendly contact. :)

I hate the limited amount of characters restricted in the comment box so I'll continue here.

Men are usually straight forward with what they want you to hear. I think you'll only strain yourself figuring him out what his subtleties mean (i know how women love to decode hidden stuff). He will let you know.

To make it easier for him, just continue what you're doing. Aware of his emotions and supportive. You said he doesn't think he's attractive? You're complimenting his looks all the while right? He doesn't believe you? Just like you don't believe us when we say "you aren't fat, you're beautiful" but it's still nice to hear.

All in all, when his "engine" is running right, he'll let you know.

Isn't waiting fun?

Ohhh that changes everything. So weird, I didn't get that at all from the reading (guy /girl difference)?

This latter part of the game is interesting because you want it to move more exclusive while he's hesitant on involving himself in another relationship. I'm sure he knows you're interested in being closer but he's got his Spartan Shield up against you.

I'll stick to my guns and still say you make the move and ask him about what he thinks about a relationship. He will reveal his concerns and if he sees you're supportive and patient. Maybe in turn will ease his doubts and fears of starting trying again through talking it out with his potential partner.

What about you, are you sure you want a "man" who is indecisive and shy? Are you the dominant type? It sounds like you are the one calling the shots while he just follows.

I know if I'm shy and un-confident it's because you've caught me at a time in my life where I'm not "running right." Maybe waiting the right decision to let him get his act together when he's better prepared and put together to handle a relationship?

Does this help?

Most people on here are teens with "why doesn't he call me problems" but I am sufficient enough to help you.

He's obviously scared of getting hurt and rejected again. The mere fact that if you ask him out will boost his confidence immensely. I don't understand why it's so difficult for women to make the move besides the fact that YOU are the one in position to get hurt but if you insist on him making the move.

Try this:
You: "are there any good movies out?

Ya I want to see X movie"

"OH ya, me too.. Maybe we can see it sometime?

Ya, how about this Friday or something?

"Ya that sounds great."

Gives him the illusion he made the move all the while it was a controlled set-up.

All in all, he just needs to feel safe and like you've stated, you have been trying to do so.

In my opinion, stop wasting dating time and just ask him out. It won't hurt his manliness or anything, like you girls... we like someone else doing the work sometimes.

Why don't you make the first move. It with help his self esteem more. I think It will give him a bigger boost of confidence if yo made it than if he made the move.

Sounds like you are going to have to make the first move. He might just be that shy.

I completely agree with That-Guy...maybe one day call him and ask if he would like to go for a drive because you are bored. I do believe that the more time you spend with them he will realize that you are interested. Especially a few outings that are instigated by you. I hope that either one of these responses helps you.